JP5524218B2 - ホログラフィック媒体製造用のプレポリマー系ポリウレタン配合物 - Google Patents
ホログラフィック媒体製造用のプレポリマー系ポリウレタン配合物 Download PDFInfo
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- JP5524218B2 JP5524218B2 JP2011529466A JP2011529466A JP5524218B2 JP 5524218 B2 JP5524218 B2 JP 5524218B2 JP 2011529466 A JP2011529466 A JP 2011529466A JP 2011529466 A JP2011529466 A JP 2011529466A JP 5524218 B2 JP5524218 B2 JP 5524218B2
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- Prior art keywords
- acrylate
- component
- isocyanate
- polyurethane composition
- meth
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 115
- 239000004814 polyurethane Substances 0.000 title claims description 36
- 229920002635 polyurethane Polymers 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000009472 formulation Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 aliphatic isocyanate Chemical class 0.000 claims description 39
- 229920005862 polyol Polymers 0.000 claims description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 35
- 150000003077 polyols Chemical class 0.000 claims description 35
- 239000012948 isocyanate Substances 0.000 claims description 28
- 150000002513 isocyanates Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 18
- 229920001451 polypropylene glycol Polymers 0.000 claims description 17
- 229920000570 polyether Polymers 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 14
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 13
- 230000001588 bifunctional effect Effects 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 5
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 5
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 5
- 229920001400 block copolymer Polymers 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229920013730 reactive polymer Polymers 0.000 claims description 2
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- 238000003384 imaging method Methods 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 24
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 23
- 239000011521 glass Substances 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 16
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 14
- 229920005906 polyester polyol Polymers 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- SQHOAFZGYFNDQX-UHFFFAOYSA-N ethyl-[7-(ethylamino)-2,8-dimethylphenothiazin-3-ylidene]azanium;chloride Chemical compound [Cl-].S1C2=CC(=[NH+]CC)C(C)=CC2=NC2=C1C=C(NCC)C(C)=C2 SQHOAFZGYFNDQX-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 10
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000011344 liquid material Substances 0.000 description 9
- 125000006850 spacer group Chemical group 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 7
- 229920000515 polycarbonate Polymers 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 6
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229960004063 propylene glycol Drugs 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 5
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 5
- 235000019437 butane-1,3-diol Nutrition 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920001610 polycaprolactone Polymers 0.000 description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000013500 data storage Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 3
- RHNNQENFSNOGAM-UHFFFAOYSA-N 1,8-diisocyanato-4-(isocyanatomethyl)octane Chemical compound O=C=NCCCCC(CN=C=O)CCCN=C=O RHNNQENFSNOGAM-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
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- 239000007983 Tris buffer Substances 0.000 description 3
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- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 3
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- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
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- 229950000688 phenothiazine Drugs 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
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- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 101150046896 trm1 gene Proteins 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Images
Classifications
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- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
A)少なくとも、もっぱらジオールをベースとするNCO末端ポリウレタンプレポリマーを含み、そのNCO基が第1級様式で結合しているポリイソシアネート成分、
B)イソシアネート反応性ポリマー
C)化学線の作用下でエチレン性不飽和化合物と重合することにより反応する基(放射線硬化性基)を有し、それ自体NCO基を含まない化合物、
D)フリーラジカル安定剤、
E)光開始剤、
F)任意に、触媒、
G)任意に、助剤および添加剤
を含むポリウレタン組成物を提供する。
1〜60wt%の本発明に必須の成分A)、
5〜93.999wt%の成分B)、
5〜70wt%の成分C)、
0.001〜10wt%の光開始剤E)、
0〜10wt%のフリーラジカル安定剤D)、
0〜4wt%の触媒F)、
0〜70wt%の助剤および添加剤G)
を含む。
10〜55wt%の本発明に必須の成分A)、
15〜79.989wt%の成分B)、
10〜70wt%の成分C)、
0.01〜7.5wt%の光開始剤E)、
0.001〜2wt%のフリーラジカル安定剤D)、
0〜3wt%の触媒F)、
0〜50wt%の助剤および添加剤G)
を含む。
15〜50wt%の本発明に必須の成分A)、
25〜69.489wt%の成分B)、
15〜50wt%の成分C)、
0.5〜5wt%の光開始剤E)、
0.01〜0.5wt%のフリーラジカル安定剤D)、
0.001〜2wt%の触媒F)、
0〜35wt%の助剤および添加剤G)
を含む。
以下の実施例は、本発明による光重合体の説明のために記載しており、限定的に理解されるべきでない。特に記載のない限り、割合はすべて、重量基準の割合に関連している。
ように調整した。
1Lフラスコに、まず、0.18gのオクタン酸スズ、374.8gのε−カプロラクトンおよび374.8gの二官能性ポリテトラヒドロフランポリエーテルポリオール(OH当量500g/mol)を仕込み、これを120℃まで加熱し、固形分(不揮発性構成成分の割合)が99.5wt%以上になるまで、この温度で保持した。この後、冷却すると、生成物がワックス状固形物として得られた。
500ml容丸底フラスコに、まず、0.1gの2,6−ジ−tert−ブチル−4−メチルフェノール、0.05gのジブチルスズジラウレート(Desmorapid Z、Bayer MaterialScience AG,Leverkusen,Germany)と、酢酸エチル中トリス(p−イソシアナトフェニル)チオホスフェート27%の溶液213.07g(Desmodur(登録商標)RFE、Bayer MaterialScience AG,Leverkusen,Germanyの製品)を仕込み、これを60℃まで加熱した。続いて、42.37gの2−ヒドロキシエチルアクリレートを滴下し、混合物は、イソシアネート含有量が0.1%未満に低下するまで60℃で保持した状態を継続した。この後、冷却し、酢酸エチルを減圧下で完全に除去した。生成物は、一部結晶性の固形物として得られた。
丸底フラスコに、まず、攪拌下、N2をパージしながら、378.0gのヘキサメチレンジイソシアネート(HDI)を仕込み、0.019gの塩化イソフタロイルを添加した。混合物を100℃まで加熱し、576.36gのAcclaim 4200(数平均モル質量4000g/molのポリプロピレンオキシド)を、3時間かけて添加した。混合物を、NCO値が18.5%NCOに達するまで攪拌し、次いで90℃まで冷却し、0.076gのビス−2−エチルヘキサン酸亜鉛を添加した。混合物を、目標理論値のNCO値(17.2%NCO)に達するまで攪拌した。次いで、室温まで冷却し、0.095gの塩化イソフタロイルを添加することにより反応を停止させた。次いで、過剰のHDIを、薄膜エバポレータを用いた蒸留により140℃で除去した(残留HDI<0.03%)。生成物は、黄色味をおびた液状物として得られる。
丸底フラスコに、まず、攪拌下、N2をパージしながら、236.25gの2,2,4−トリメチルヘキサメチレンジイソシアネート(TMDI)を仕込み、0.008gの塩化イソフタロイルを添加した。混合物を100℃まで加熱し、167.67gのAcclaim 2200(数平均モル質量2000g/molのポリプロピレンオキシド)を、3時間かけて添加した。混合物を、NCO値が21.8%NCOに達するまで攪拌し、次いで90℃まで冷却し、0.077gのビス−2−エチルヘキサン酸亜鉛を添加した。混合物を、目標理論値のNCO値(20.3%NCO)に達するまで攪拌した。次いで、室温まで冷却することにより反応を停止させた。次いで、過剰のHDIを、薄膜エバポレータを用いた蒸留により140℃で除去した(残留HDI<0.12%)。生成物は、無色の液状物として得られる。
400gのHDI(ヘキサメチレンジイソシアネート)および0.06gのオクタン酸亜鉛を、まず、攪拌しながら110℃で、4l容4つ口フラスコに仕込む。1.5時間以内に、1570gの二官能性ポリプロピレングリコール(数平均モル質量8000g/mol)を、115℃の温度が維持されるような様式で添加する。同温度で、さらに2時間後、0.06gのリン酸ジブチルを添加し、次いで、混合物を75℃まで冷却する。この温度で、混合物を濾過する。次いで、700gのHDI(ヘキサメチレンジイソシアネート)と0.5gの塩化ベンゾイルを添加する。続いて、過剰のHDIを、薄膜蒸留によって、130℃および0.1トールにて留去する。得られたプレポリマーは、1.92%のNCO含有量およびほぼ8000mPas(25℃)の粘度を有する。
1300gのHDI(ヘキサメチレンジイソシアネート)、1.3gの塩化ベンゾイルおよび1.3gのパラ−トルエンスルホン酸メチルを、まず、攪拌しながら、4l容4つ口フラスコに仕込む。3時間以内に、1456gの二官能性ポリプロピレングリコールポリエーテル(2000g/molの数平均分子量を有する)を80℃で添加し、混合物を同温度でさらに1時間攪拌する。続いて、過剰のHDIを薄膜蒸留によって、130℃および0.1トールで留去した。得られたプレポリマーは、3.23%のNCO含有量および1650mPas(25℃)の粘度を有する。
8.89gのポリオール1(上記のようにして調製)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、1.647gのDesmodur(登録商標)XP2410(成分Aとの比較)を添加し、混合物を再度混合した。最後に0.009gのFomrez UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0101.
6.117gのポリオール2(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、4.418gのBaytec(登録商標)WE 180(成分Aとの比較)を添加し、混合物を再度混合した。最後に0.030gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0063.
7.743gのAcclaim(登録商標)4200(数平均モル質量4000g/molのポリプロピレンオキシド)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、2.792gのDesmodur(登録商標)XP 2599(成分A)を添加し、混合物を再度混合した。最後に0.0245gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0158.
5.63gのポリエーテルL5050(エチレンオキシドおよびプロピレンオキシドから形成された二官能性コポリエーテル,エチレンオキシド成分の合計50wt%,当量984.2g/mol)(成分B)を、4.50gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、4.154gのDesmodur(登録商標)XP 2599(成分A)を添加し、混合物を再度混合した。最後に0.0323gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0142.
7.554gのAcclaim(登録商標)4220N(エチレンオキシドキャップ型数平均モル質量4000g/molのポリプロピレンオキシド)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、2.983gのDesmodur(登録商標)XP 2599(成分A)を添加し、混合物を再度混合した。最後に0.0071gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0141.
6.128gのAcclaim(登録商標)4200(数平均モル質量4000g/molのポリプロピレンオキシド)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、4.408gのプレポリマー1(成分A)を添加し、混合物を再度混合した。最後に0.0150gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0147.
6.965gのAcclaim(登録商標)4200(数平均モル質量4000g/molのポリプロピレンオキシド)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、3.570gのプレポリマー2(成分A)を添加し、混合物を再度混合した。最後に0.0293gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0150.
4.819gのAcclaim(登録商標)4200(数平均モル質量4000g/molのポリプロピレンオキシド)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、5.716gのプレポリマー3(成分A)を添加し、混合物を再度混合した。最後に0.0252gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0211.
5.497gのAcclaim(登録商標)2200(数平均モル質量2000g/molのポリプロピレンオキシド)(成分B)を、3.75gのウレタンアクリレート1(成分C)、0.15gのCGI 909および0.015gの新メチレンブルー(成分Eも一緒)(60℃)、および0.525gのN−エチルピロリドン(成分G)と、透明な溶液が得られるように混合した。続いて、混合物を30℃まで冷却し、1.783gのDesmodur(登録商標)XP 2599および3.254gのプレポリマー4(成分Aも一緒)の混合物を添加し、混合物を再度混合した。最後に0.030gのFomrez(登録商標)UL 28(成分F)を添加し、混合物を短時間、再度混合した。次いで、得られた液状物質をガラスプレートに適用し、これに第2のガラスプレートを被せ、該プレート間の間隔はスペーサーによって20μmに維持した。この試料試験片を室温で放置し、16時間かけて硬化させた。最大Δn:0.0168.
Claims (12)
- A)もっぱらジオールをベースとするNCO末端ポリウレタンプレポリマーを少なくとも含み、そのNCO基が第1級様式で結合しているポリイソシアネート成分、
B)1分子当たり平均少なくとも1.5個のイソシアネート反応性基を有する多官能性イソシアネート反応性ポリマー
C)ウレタンアクリレートおよび/またはウレタンメタクリレート、
D)フリーラジカル安定剤、
E)光開始剤、
F)任意に、触媒、
G)任意に、助剤および添加剤
を含むポリウレタン組成物。 - ウレタン、アロファネート、ビウレットおよび/またはアミド基を有するNCO官能性プレポリマーがA)において用いられることを特徴とする、請求項1に記載のポリウレタン組成物。
- A)において用いられるイソシアネート官能性プレポリマーが、脂肪族イソシアネート官能性化合物と、500〜8500g/molの数平均モル質量を有するオリゴマーポリオールまたはポリマーポリオールまたはポリアミンとから形成されるウレタン、アロファネートまたはビウレットであることを特徴とする、請求項1または2に記載のポリウレタン組成物。
- A)において用いられるイソシアネート官能性プレポリマーが、HDIまたはTMDIと、1000〜8200g/molの数平均モル質量を有する二官能性ポリエーテルポリオールとから形成されるアロファネートであることを特徴とする、請求項1〜3のいずれかに記載のポリウレタン組成物。
- A)においてイソシアネート官能性プレポリマーとして用いられる化合物は、0.5wt%未満の遊離モノマーイソシアネートの残存含有量を有することを特徴とする、請求項1〜4のいずれかに記載のポリウレタン組成物。
- エチレンオキシドおよび/またはプロピレンオキシドをベースとするホモポリマーまたはランダムコポリマーまたはブロックコポリマーが、任意に、モノマー単位としてテトラヒドロフラン、ブチレンオキシド、またはε−カプロラクトンと組合せて、1.5〜6のOH官能価および200〜18000g/molの数平均モル質量で、成分B)において用いられることを特徴とする、請求項1〜5のいずれかに記載のポリウレタン組成物。
- 成分C)に用いられる化合物が>1.55の屈折率nD 20を有することを特徴とする、請求項1〜6のいずれかに記載のポリウレタン組成物。
- 芳香族イソシアネートおよび2−ヒドロキシエチルアクリレート、ヒドロキシプロピルアクリレート、4−ヒドロキシブチルアクリレート、ポリエチレンオキシドモノ(メタ)アクリレート、ポリプロピレンオキシドモノ(メタ)アクリレート、ポリアルキレンオキシドモノ(メタ)アクリレート、およびポリ(ε−カプロラクトン)モノ(メタ)アクリレートをベースとするウレタンアクリレートおよびウレタンメタクリレートが成分C)に用いられることを特徴とする、請求項1〜7のいずれかに記載のポリウレタン組成物。
- 請求項1〜8のいずれかに記載のポリウレタン組成物を基材または鋳型に適用し、硬化させる、可視ホログラムを記録するための媒体の製造方法。
- 請求項9に記載の方法により得られる可視ホログラムを記録するための媒体。
- 光学部材として、画像、または画像形成もしくは画像投影のための請求項10に記載の媒体の使用。
- 請求項10に記載の媒体を用いるホログラムを記録するための方法。
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2009
- 2009-09-24 KR KR1020117007457A patent/KR101720807B1/ko active IP Right Grant
- 2009-09-24 KR KR1020177007648A patent/KR101808493B1/ko active IP Right Grant
- 2009-09-24 US US13/122,005 patent/US8852829B2/en active Active
- 2009-09-24 JP JP2011529466A patent/JP5524218B2/ja active Active
- 2009-09-24 EP EP09778689.1A patent/EP2342249B1/de active Active
- 2009-09-24 CA CA2738835A patent/CA2738835A1/en not_active Abandoned
- 2009-09-24 RU RU2011116997/04A patent/RU2515549C9/ru not_active IP Right Cessation
- 2009-09-24 WO PCT/EP2009/006890 patent/WO2010037496A1/de active Application Filing
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KR20110079631A (ko) | 2011-07-07 |
BRPI0920781A2 (pt) | 2015-12-22 |
EP2342249A1 (de) | 2011-07-13 |
WO2010037496A1 (de) | 2010-04-08 |
RU2515549C2 (ru) | 2014-05-10 |
KR20170034453A (ko) | 2017-03-28 |
US8852829B2 (en) | 2014-10-07 |
JP2012504665A (ja) | 2012-02-23 |
CA2738835A1 (en) | 2010-04-08 |
EP2342249B1 (de) | 2017-10-25 |
RU2011116997A (ru) | 2012-11-10 |
US20110189591A1 (en) | 2011-08-04 |
KR101720807B1 (ko) | 2017-03-28 |
RU2515549C9 (ru) | 2014-09-20 |
KR101808493B1 (ko) | 2017-12-12 |
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